Sulphur dyestuffs



Patented May 20, 1930 UNITED STATES PATENT OFFICE BI S-WIN KRAMER, OF COLOGNE-DEUTZ, IBERNI IARD BOLLWEGrOF LEVERKUSEN-ON-THE- RHINE, AND LUDWIG ZEH, OF WIESDORF-ON-THE RHINE, GERMANY, ASSIGNORS TO GENERAL ANILINE WORKS, INC. OF NEW YORK, IN. Y., ACORPORATION OF DELA- SULPHUR Dress-urns No Drawing. Application filed June 21, 1928, Serial 110,237,343, and in Germany August 31, 1927. i

' This invention relates to the manufacture of technically valuable reddish brown sul- 1 phur dyestuffs and to the new products obtainable thereby. 5 The process of manufacture in accordance with this invention is carried out by heating B-binaphthol of the formula i on with a sulphur halide, or a mixture of a sulphur halide and sulphur. A diluent such as an indifferent solvent of a high boiling point A may be used, for example nitrobenzene, 2b trichlorobenzene, dichlorobenzene, etc.

The new products are generally dark powders difiicultly soluble in the usual organic solvents andmconcentrated sul huric acid, in the latter generally with a violet coloration, easily soluble in aqueous sodium sulfide solutions with a brownish-red coloration, dyeing cotton after ex sure to air pure reddish-brown shades 0 good fastness.

The following examples illustrate the invention:

Example 1.-2O parts by weight of 3-binaphthol are slowly stirred into 46 arts by weight of sulphur mono chloride, Cl at about 60-100 C. when a vigorous reaction takes place accompanied by the evolution of hydrogen chloride. When the reaction has subsided the temperature is raised to about '250-260 C. and maintained for about 4 hours. A second reaction takes place with .40 frothin the melt becomes viscous and finally fairly ry. The dyestufl' is purified by dissolving in a sodium sulfide'solution and precipitation. The dark brown powder obtained dissolves in water with the addition of sodium sulfide with a brownish red coloration, dyes the fibre in shades of the same color and after exposure to the air becomes reddishbrown. v

By keeping the temperature of the sul- 50 phurization ower or'carrying out the restuff is obtained.

-Emam pZe'.2.-2O parts by weight of ,B-binaphthol are introduced at 80100 G. into a mixture of 46 arts by Weightof, sulphur mono chloride. Cl and 20 parts by weight of sulphur and further treated in accordance with the directions of Example 1. The resulting dyestulf produces yellower shades than that obtained according to Example 1.

Example 3.20 parts by Weight of 'fi-binaphthol are dissolved in 150 parts by weight of trichlorobenzene and into this solution at about 80-120 G. 46 parts by weight of sulphur mono chloride, sgclg are stirred. After some time the mixture is heated to boiling for seven hours. The product is a dark powder soluble in aqueous sodium sulfide with a brownish-red coloration, dyeing cotton reddish-brown shades.

We claim 1. In the process for the manufacture of sulphur dyes the step which comprises treating B-binaphthol with acompound of the group consisting of sulphur halogenides and mixtures of sulphur with sulphur halogenides at a temperature of about 250- 260 C.

2. In the process for the manufacture of sulphur dyes the step which comprises heating fl-binaphthol with a sulphurhalide at a temperature of about 250260 C.

3. In the process for the manufacture of sulphur dyes the step which comprises heating ,B-binaphthol with a sulphur halide and sulphur at a temperature of about 250- 260 C. y

4. In the process for the manufacture of sulphur dyes the ste which comprises heat-' ing fl-binaphthol with a compound of the group consisting of sulphur halogenides and mixtures of sulphur with sulphur halogenides and a high boiling indifferent organic solvent to the boiling point of the solvent.

5. In the process for the manufacture of sulphur dyes the stepwhich comprises heating'B-binaphthol with a sulphurhalide and a high boiling indiflerent organic solvent to the boiling point of the solvent.

organic solvents and in strong sulphuric acid, easily soluble in aqueous sodium sulfide solution with brownish-red coloration, from which solution cotton is dyed to reddishbrown shades of d fast-ness roperties.

8. The new su phur dyestuif obtainable by treating ,B-binaphthol with sulphur monochloride in trichlorobenzene, said dyestufi beinga dark powder, soluble in aqueous sodium sulfide solution with a, brownish red coloration from which solution cotton is dyed a reddish brown shade.

- In testimony whereof we have hereunto set our hands.

ERWIN KRAMER. [L 5.] BERNHARD BOLLWEG. [1,. s.] LUDWIG ZEH. I [L 8.] 

